Sodium Carbonate → HCID 19911439, compound

HRID 1533926Notes

Reaction equation

HRID 1533926 reaction equation
[CH2:1]([C:3]1[CH:4]=[C:5]([N:9]2[CH2:14][CH2:13][NH:12][CH2:11][CH2:10]2)[CH:6]=[CH:7][CH:8]=1)[CH3:2].[Cl:15][CH2:16][CH2:17][CH:18]1[O:22][C:21](=[O:23])[N:20]([CH3:24])[CH2:19]1.C(=O)([O-])[O-].[Na+].[Na+]>C(O)CCC.[I-].[K+]>[ClH:15].[ClH:15].[CH2:1]([C:3]1[CH:4]=[C:5]([N:9]2[CH2:10][CH2:11][N:12]([CH2:16][CH2:17][CH:18]3[O:22][C:21](=[O:23])[N:20]([CH3:24])[CH2:19]3)[CH2:13][CH2:14]2)[CH:6]=[CH:7][CH:8]=1)[CH3:2]

Participants

6

Reactant 3

HCID 10340Sodium CarbonateHCID 146987465-(2-Chloro-ethyl)-3-methyl-oxazolidin-2-oneHCID 199114731-(3-Ethylphenyl)piperazine

Product 1

HCID 19911439HCID 19911439, compoundYield 139.7%

Reagents, catalysts & solvents 2

HCID 4875Potassium IodideCatalystHCID 2631-ButanolSolvent

Procedure

A mixture of 12.2 g (0.064 mol) of 1-(3-ethylphenyl)piperazine, 12.6 g (0.077 mol) of 5-(2-chloroethyl)-3-methyl-2-oxazolidinone, 27.1 g (0.255 mol) of anhydrous sodium carbonate, and 0.5 g (0.003 mol) of potassium iodide in 300 mL of 1-butanol was heated at reflux for 16 h. The mixture was concentrated under reduced pressure and the residue partitioned between 300 mL of benzene and 300 mL of water. The benzene layer was washed with water and brine, dried (MgSO4) and concentrated under reduced pressure to yield 21.0 g (100%) of a gold-colored, viscous oil.

Workup

  1. temperaturewas heated
  2. temperatureat reflux for 16 h
  3. concentrationThe mixture was concentrated under reduced pressure
  4. customthe residue partitioned between 300 mL of benzene and 300 mL of water
  5. washThe benzene layer was washed with water and brine
  6. dry with materialdried (MgSO4)
  7. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-eb28ad34538d45dfb58fdff58c3978d1
Source dataset
uspto-grants-1992_02
Patent number
US05086055

Reaction notes

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